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Jon Hirschtick founded SolidWorks in 1993, with the goal of building 3D CAD software that was easy-to-use, affordable, and available on the Windows desktop. Today, the company has sold billions of dollars worth of CAD/CAM software and continues as part of Dassault Systemes, a company that acquired SolidWorks in 1997. Several years after the acquisition, Jon transitioned out of the CEO role and promoted his long-term partner in building SolidWorks and a great business leader, John McEleney, as CEO after achieving a run rate of $100M in revenue in 2001. In 2011, Jon Hirschtick decided to leave SolidWorks to begin the next phase of his career founding another equally high-potential company, OnShape. Not surprisingly, he brought John McEleney with him as a partner from day one. This is a story of thoughtful partnership that has endured and is repeating success.

Constant Contact: Gail Goodman

And just because it’s tough, doesn’t mean that every founder will fail to scale UP – especially if they are willing to acknowledge the harsh truths about what is actually holding back their personal development. Case in point: under CEO Gail Goodman’s leadership, Constant Contact, which provides online marketing services to small businesses and has grown to some $285 million in annual revenue since it was founded in 1998.

Gail has been at the helm of her company for all of its 15 years and running, which is no small feat. During a recent Startup Secrets session we asked her what her secret was to scaling herself at the rate that her business was growing, she shared this key piece of advice: “You have to face yourself,” she says. “You have to be unbelievably ruthless about what’s working and what’s not working. As CEO, you will have to change hundreds of times to face the different challenges in the different stages your business will go through.”

The rub is that many founders share a common characteristic that is invaluable in a company’s early days: drive. “But being relentless in your perseverance can eventually become an obstacle to change,” says Gail.

Gail, for example, played a key role in product management when Constant Contact was in its early days. She was good at and she was comfortable in that role. Only, as the company grew, she continued to be involved in the day-to-day product decisions. It wasn’t until one of her employees, the head of engineering, took her out to lunch and confronted her with the truth – that she needed to let other people step up – that she realized she had been neglecting other critical areas the company needed her to focus on. “The single biggest investment you can make as CEO is where you spend your time,” she says, “and spending time where I was comfortable was a mistake.”

You can watch the panel discussion with Stephan, Jon and Gail below:

The point of these stories is that while it’s rare to see innovators evolve into operators, it is possible to do as Stephan, Gail and of course many other legends such as Bill Gates show us. It means you need to be excited about the challenge of constantly changing and evolving. At the same time, there are plenty of examples of founders who have no interest in running a later stage company and there’s nothing wrong with that either. For what’s it’s worth as an investor, it really matters to me to see founders stay really engaged building the company, no matter their role or title. However, in the end, there’s no one-size-fits all strategy out there. What matters is what choice YOU, as a founder, want to make over time.

In his role at North Bridge Venture Partners, Michael partners with entrepreneurs helping them from inception to company to market leader. As a VC, Michael has backed and built teams that have created billions of dollars of value while focusing on large, market-changing technologies and disruptive business models such as SaaS, Cloud Computing, Open Source and Mobile. Current representative investments include Acquia, Apperian, Demandware (NYSE:DWRE), Salsify, RIFTio and Unidesk, as well as Actifio and Revolution Analytics.